Tributylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetate

HRID 1391754Notes

Reaction equation

HRID 1391754 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:12])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=1.O[C:14]1[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:16]([CH3:27])[CH:15]=1.P(CCCC)(CCCC)CCCC>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([O:12][C:14]2[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:16]([CH3:27])[CH:15]=2)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 586298591-(6-Bromopyridin-2-yl)butan-1-ol

Product 1

HCID 58629817Ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetateYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(6-bromo-2-pyridinyl)-1-butanol (626 mg, 2.72 mmol) and ethyl (4-hydroxy-2-methylphenoxy)acetate (539 mg, 2.56 mmol) in dry THF (51 mL) at 0° C. (ice/water bath) under nitrogen was added ADDM (1.32 g, 5.13 mmol) followed by nBu3P (1.28 mL, 4.95 mmol) drop-wise. The mixture was stirred with slow warming to rt over 18 hours and then concentrated under vacuum, diluted with EtOAc (150 mL) and washed with water (3×75 mL), dried (Na2SO4), filtered and reduced to give a yellow oil. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 20:1 to 10:1) afforded the title compound (388 mg).

Workup

  1. concentrationconcentrated under vacuum
  2. additiondiluted with EtOAc (150 mL)
  3. washwashed with water (3×75 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customto give a yellow oil
  7. customPurification by SPE (silica, 20 g cartridge)
  8. washeluting with cyclohexane

Sources & evidence

ORD record
ord-bf7c010e2c6e464a9cf2cf92484e428c
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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